As many enzymes and cell surface receptors possess handedness, the enantiomers of a racemic pair of compounds may be adsorbed, activated, and/or degraded in different manners. In some instances, two enantiomers of a given racemic drug may have different or even opposite pharmacological activities. This aspect in conjunction with other factors within the pharmaceutical industry have stimulated the need for enantiomerically pure intermediates and bulk optically active compounds. Quick access to reasonable amounts of enantiomerically pure materials to assess their pharmaceutical activity is highly desirable to many pharmaceutical companies. Among the asymmetric technologies developed to analyze and separate optically active compounds, the direct separation of enantiomers by HPLC on enantioselective stationary phases has been a subject of intense investigation. As a result, a wide variety of enantioselective stationary phases have been developed. Although a thorough evaluation of all the current enantioselective columns is impossible, the commonly used ones do seem to have their limitations. It is fair to say that the chiral resolution of racemic materials remains a major challenge. This proposal in intended for the rapid development of more efficient stationary phases for enantioselective chromatography. Specifically, parallel combinatorial libraries are proposed for the development of enantioselective stationary phases. These methods will be applied to develop efficient enantoselective stationary phases for separating racemates of several compounds of pharmaceutical importance.